Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2,2'-Bipyridine | HCID 1474 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Cyclopropylboronic acid | HCID 2760897 | — |
| Reactant | methyl 1H-pyrrole-3-carboxylate | HCID 12361759 | — |
| Catalyst | Cupric acetate | HCID 8895 | — |
| Product | HCID 86703246 | HCID 86703246 | 57.1% |
Reaction Steps
A mixture of methyl 1H-pyrrole-3-carboxylate (500 mg, 4.00 mmol), cyclopropylboronic acid (686 mg, 7.99 mmol), copper(II) acetate (726 mg, 4.00 mmol), 2,2′-bipyridyl (624 mg, 4.00 mmol), sodium carbonate (847 mg, 7.99 mmol) was stirred at 70° C. for 16 hr, concentrated, diluted in EtOAc/water, and extracted twice with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), and concentrated. The crude material was purified by silica gel column chromatography (hexane/EtOAc 4:1) to afford the title compound (377 mg, 57% yield) as a yellow oil. TLC (hexane/EtOAc 4:1): Rf=0.26.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09365576B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-4c7e14684c724464a6b260b1f0257719 |
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| Source note | uspto-grants-2016_06 |
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